1 Answer
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Internode (an iiNet for that matter) are very fussy when using SmartHosts. Even though you're authenticating with your username and password, because your email is not being sent from an @internode from address, they may be rejecting your email.

I had this happen with iiNet, on a business account. They were happy to open up Port 25 inbound, but wouldn't help me with sending emails via the Exchange smarthost. Also, the IP address they gave me had bad history so I couldn't even just send via MX.

Interesting that it works via non-secure though, so I could be way off the ball here.

If you find it's not this, and something else, please let me know as I'd be interested to try it for iiNet.

For me, the issue has never been about using a smarthost with internode. In fact, I'm using/have been for years (using it with Exchange 2003). I'm just doing it over port 25 .. and not port 465. I'm not sure if I can tell exchange 2010 to use SSL for a smarthost. I've set the port via command line .. i've set the auth details (which i'm assuming I've ticked the correct box). Hmm....
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Pure.KromeJun 29 '10 at 3:46